10 Interview Questions That Get to the Heart of Things

Some see the interview process as an art form, one that allows you to carefully coax candidates out of their shells and reveal a true glimpse of their personality. Others see it as a necessary evil full of polished answers and wasted formalities.

The truth is that you’ll never truly know a candidate until they have worked for you. Getting references certainly helps, but it’s difficult to get to the bottom of things in a first interaction. That being said, asking the right questions can help you cut past the practiced responses and get to the core of someone’s motivation, skills and strengths.

Below are 10 interview questions that really expose a candidate’s philosophies on work, along with explanations on how to interpret the answers they provide:

1. Tell Me a Little About Yourself

What you’re listening for: How do the candidates describe themselves? What are the things they stress above all others? Some candidates may phrase this answer in relation to other people in their lives (i.e. “I’m the mother of two children”), or they may frame the question based on their professional experience (i.e. “I’m a media-relations guru”). However they answer, candidates should be confident, concise and able to relate some of their description to the job at hand. This also gives you the opportunity to evaluate whether or not they would be a good culture fit.

2. Why Should We Hire You? (Or Why Do You Want This Job?)

What you’re listening for: This is an opportunity for the candidates to demonstrate the research they’ve done regarding the position and your organization, and to highlight their strengths in relation to your needs. The candidate should be able to make a compelling case as to what sets him or her apart from the competition. Remember that this is the opportunity for candidates to do more than regurgitate their resume. You’re looking for creative solutions, resilience, enthusiasm and a mix of experiences that can contribute a unique perspective.

3. If I Reached Out to Your References, What Would Your Last Supervisor Say Is the Area in Which You Most Need Improvement?

What you’re listening for: This is another way to approach the classic “What’s your greatest weakness?” question without directly asking the candidate to reveal their flaws. By imagining they are speaking from a former supervisor’s perspective, candidates may offer more honest feedback on the impression that their previous boss may have had.

4. Tell Me What Frustrates You

What you’re listening for: While any job has its frustrations, you want candidates to be able to speak coherently about the things that they may find challenging in the course of the workday. Pay attention to what they focus on. Obviously, if their frustration reflects a daily reality the job (for example, if the candidate hates working without clear direction, but the role will be largely independent and unstructured), it may be a red flag that the issues will continue into their new position. If the candidate describes a handful of minor issues, this may foreshadow an inability to handle larger obstacles or stressful situations on the job. You also want to ask candidates how they handled their frustration and make sure that they handled it at an appropriate time and in the right way (for example, they didn’t let a disagreement affect the productivity of their team).

5. Why Did You Leave Your Last Job?

What you’re listening for: The candidate should be able to explain why he or she chose to leave his or her last job without defaming the employer or speaking overly negative about the company. The answer should focus on the candidate’s own goals to further his or her career or take on a new challenge.

6. What Do You Know About Our Company?

What you’re listening for: No matter what your business is, a candidate should be familiar with what you do, the customers you serve and what differentiates you from similar businesses. If you have a strong online presence, candidates should have visited your website and even be able to offer feedback. You are also looking for enthusiasm when discussing your company; the candidate should express interest in what you do and eagerness to become a part of your overall mission.

7. Describe the Best Supervisor/Boss You Ever Reported To

What you’re listening for: This question will reveal how the candidate views interpersonal relationships and what personality type or leadership style he or she will thrive under. This question is as much for candidates to demonstrate their personality type as it is for you to determine if the manager they may work for is the right personality fit.

8. What Is the Most Difficult Decision You Ever Had to Make at Work in the Last Year?

What you’re looking for: It’s important that candidates can offer a legitimately difficult circumstance in which they used solid judgment, critical thinking and problem-solving skills under pressure. You’re looking out for a candidate who weighed different sides of an issue, and how it affected their co-workers, their companies and themselves. If they don’t have a solid example, consider that a red flag.

9. What Questions Do You Have for Us?

What you’re listening for: First and foremost, you want the candidate to demonstrate curiosity in your company. Look out for a candidate that asks an obvious question (e.g. “What exactly does this company do?”). This part of the interview may also give candidates another chance to further highlight their specific experience and how it is a right fit for the job. You may also consider it a good sign if the candidate asks a question that references something mentioned in the beginning of the interview. Asking this question toward the end of the interview normally generates more candid answers, as you and the candidate have developed a rapport throughout the course of the conversation.

10. Where Do You See Yourself in Five Years?

What you’re listening for: In most cases, you won’t necessarily be expecting candidates to assure you that they will still be in the same exact position five years down the line. What you’re really hoping to hear is a clear plan with defined goals that demonstrates how ambitious they are. Unless you’re looking for an extremely long-term, unchanging position, look for an honest answer about how excelling in this position will help them pursue their own personal career goals while helping your business grow.

Interviewing can be very stressful, time-consuming and tedious. However, it’s also often the only opportunity you have to evaluate a candidate face-to-face and to make sure they are not only interested in the position, but can communicate well and are equally as passionate about what your business does. The 10 questions above should help to identify candidates with the drive and ambition to elevate your company to the next level. To learn more about the hiring process, click here.

Megan has worked in the advertising and digital media space for over ten years, writing everything from content briefs to press releases to advertising copy. Industries she has worked in include: human resources, print media, digital media, computer software, online advertising and entertainment.